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Forging Fluorine-Containing Quaternary Stereocenters by a Light-Driven Organocatalytic Aldol Desymmetrization Process
Sara Cuadros1, Luca Dell'Amico1, Paolo Melchiorre2,1
1ICIQ-Institute of Chemical Research of Catalonia the Barcelona Institute of Science and Technology, Avenida Països Catalans 16, 43007, Tarragona, Spain.
Abstract:
Reported herein is a light-triggered organocatalytic strategy for the desymmetrization of achiral 2-fluoro-substituted cyclopentane-1,3-diketones. The chemistry is based on an intermolecular aldol reaction of photochemically generated hydroxy-o-quinodimethanes and simultaneously forges two adjacent fully substituted carbon stereocenters, with one bearing a stereogenic carbon-fluorine unit. The method uses readily available substrates, a simple chiral organocatalyst, and mild reaction conditions to afford an array of highly functionalized chiral 2-fluoro-3-hydroxycyclopentanones.
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